Hi Guys,
I'm a US Citizen who worked in Canada after retiring from the Navy several years ago and married a Canadian citizen, eventually becoming a Canadian Permanent Resident. I lived and worked in Canada for about 5 years (non-aviation career) and converted my FAA CPL to a Transport Canada ticket while up there.
I have moved back to the US and currently fly for a regional, but because my Mother in Law's health, my wife and I may be returning to Canada in the future. Because of this, I've been actively looking into what it takes to convert my current ATP and the two type ratings I've earned since being back in the US.
What I've found out is that a couple of years ago, Transport Canada and the FAA made the process of "trading" licenses much easier, and now they will allow all type ratings to transfer over which they did not use to do without additional testing. Here's the Transport Canada link for additional information:
Conversion between U.S. and Canadian Pilot Licences
Working in Canada is another story. If you are not a citizen or permanent resident of Canada, or the holder of a foreign worker work permit, you can't be hired. In order for a Canadian company (airline) to hire a foreign worker, they have to submit a request to Human Development Recource Canada which attempts to prove that there are simply not enough qualified people currently in Canada to fill the need. Once HRDC approves the need, the company can then actively recruit foreign workers. Then, if you look like a good candidate, they apply for a foreign worker work permit to Immigration Canada, which can take months.
Unfortunatly this process is very slow, and does not favor hiring US pilots without ties to Canada. However, IF the pilot pool up there gets tight, they may start actively recruiting.
A couple of other quick notes: the Canadian dollar is currently about 1.2 to the US dollar, so 30K is roughly 25K USD in spending power. Also, if you are luck enough to get a look from a Canadian company, your background check and knock you out of the running. Immigration Canada is ANAL about any type of law enforcement action in your past.
Fly safe.